Triethylamine → 3-(N-(N',N'-dimethylaminoethane)carbamoyl)cholesterol

HRID 1385824Notes

Reaction equation

HRID 1385824 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.[CH3:14][C@@H:15]([C@@H:22]1[C@@:26]2([CH3:44])[CH2:27][CH2:28][CH:29]3[C@@:34]4([CH3:43])[CH2:35][CH2:36][CH:37]([O:39][C:40](Cl)=[O:41])[CH2:38][C:33]4=[CH:32][CH2:31][CH:30]3[CH:25]2[CH2:24][CH2:23]1)[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20]>ClCCl.O1CCOCC1>[CH3:14][C@@H:15]([C@@H:22]1[C@@:26]2([CH3:44])[CH2:27][CH2:28][C@@H:29]3[C@@:34]4([CH3:43])[CH2:35][CH2:36][C@H:37]([O:39][C:40]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[O:41])[CH2:38][C:33]4=[CH:32][CH2:31][C@H:30]3[C@@H:25]2[CH2:24][CH2:23]1)[CH2:16][CH2:17][CH2:18][CH:19]([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 54236888C28H45ClO2

Product 1

HCID 1152343-(N-(N',N'-dimethylaminoethane)carbamoyl)cholesterol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-dimethylaminoethylamine (19.40 mg, 24:1, 0.22 mmol) and triethylamine (310 μl, 2.23 mmol) in dichloromethane (3 ml) at room temperature was slowly added a solution of cholesteryl chloroformate (100 mg, 0.22 mmol) in 1,4-dioxane. When the reaction was completed, the mixture was evaporated to dryness and the residue was purified by flash chromatography (CHCl3/MeOH, 4:1). A white solid was obtained, yield 105 mg (95%). The structure was verified by NMR and MALDI.

Workup

  1. customthe mixture was evaporated to dryness
  2. customthe residue was purified by flash chromatography (CHCl3/MeOH, 4:1)
  3. customA white solid was obtained

Sources & evidence

ORD record
ord-7b98b13705b842f6a0bcedff9f433bd4
Source dataset
uspto-grants-2001_07
Patent number
US06264917B1

Reaction notes

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